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Fort Myers Cruises, Sailing & Water Tours

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Fort Myers Tours

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Fort Myers Beach 1.5hr Jet Ski Dolphin Tour

Discover the natural beauty of Southwest Florida from the seat of your own Sea-Doo on an exciting 1.5-hour guided dolphin eco-tour. Follow your experienced guide …More

5.0 (2)

Fort Myers Beach 1.5hr Jet Ski Dolphin Tour

Discover the natural beauty of Southwest Florida from the seat of your own Sea-Doo on an exciting 1.5-hour guided dolphin eco-tour. Follow your experienced guide...

2 hours • Free Cancellation
5.0 (2)
from
$225
Private Lake Okeechobee Bass Charter Near Naples

Escape the beaches and discover one of the world's most legendary bass fisheries on a private Lake Okeechobee fishing charter, conveniently accessible from Naples. Known …More

Likely to Sell Out
Likely to Sell Out
5.0 (26)

Private Lake Okeechobee Bass Charter Near Naples

Escape the beaches and discover one of the world's most legendary bass fisheries on a private Lake Okeechobee fishing charter, conveniently accessible from Naples. Known...

4 hours • Free Cancellation
5.0 (26)
from
$169
Private Lake Okeechobee Bass Charter Near Fort Myers

Leave the Gulf Coast behind and discover one of the world's greatest bass fishing destinations on a private Lake Okeechobee fishing charter near Fort Myers. …More

5.0 (11)

Private Lake Okeechobee Bass Charter Near Fort Myers

Leave the Gulf Coast behind and discover one of the world's greatest bass fishing destinations on a private Lake Okeechobee fishing charter near Fort Myers....

4 to 6 hours • Free Cancellation
5.0 (11)
from
$161
Private Dolphin & Sightseeing Boat Day Tour

This is the Day-Tour to our widely popular Sunset & Dolphin Boat Tour. You will get very close to wildlife and our first mate will …More

5.0 (14)

Private Dolphin & Sightseeing Boat Day Tour

This is the Day-Tour to our widely popular Sunset & Dolphin Boat Tour. You will get very close to wildlife and our first mate will...

4 hours • Free Cancellation
5.0 (14)
from
$161
Private ONLY Dolphin Boat Tours

For the price of a boat rental plus fuel, you will get a guided boat tour by our Master Captain with deep insight knowledge of …More

5.0 (34)

Private ONLY Dolphin Boat Tours

For the price of a boat rental plus fuel, you will get a guided boat tour by our Master Captain with deep insight knowledge of...

3 to 4 hours • Free Cancellation
5.0 (34)
from
$160
Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the …More

5.0 (11)

Sunset Sail in the Gulf of Mexico for up to 6 Guests

Sailing aboard a modern 38' sailboat, this sunset cruise offers a unique chance to witness the romantic beauty of the Gulf of Mexico as the...

2 hours 30 minutes • Free Cancellation
5.0 (11)
from
$149
2.5 hr Sailboat Tour aboard Orion's Child

Cool SWFL Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple …More

Likely to Sell Out
Likely to Sell Out
5.0 (92)

2.5 hr Sailboat Tour aboard Orion's Child

Cool SWFL Special Sail. SEE OUR WEBSITE for other options and availability. Since 2009, we offer the cleanest, safest, and best maintained sailing vessel. Multiple...

2 hours 30 minutes • Free Cancellation
5.0 (92)
from
$130
Fort Myers Beach #1 Parasailing Experience

Take off and enjoy the highest Fort Myers Beach parasailing flights that Wind and Water Sports has to offer! All while being captivated by amazing …More

5.0 (15)

Fort Myers Beach #1 Parasailing Experience

Take off and enjoy the highest Fort Myers Beach parasailing flights that Wind and Water Sports has to offer! All while being captivated by amazing...

1 hour • Free Cancellation
5.0 (15)
from
$110
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party …More

Likely to Sell Out
Likely to Sell Out
4.9 (55)

Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages, take pics, get some sun, make friends, play party...

3 hours • Free Cancellation
4.9 (55)
from
$89
Kayak Eco Tour in Don Pedro Island

Discover the wonders of Don Pedro Island! Dive into adventure on a kayaking eco tour with the areas most experienced tour guides. Your tour guide …More

5.0 (160)

Kayak Eco Tour in Don Pedro Island

Discover the wonders of Don Pedro Island! Dive into adventure on a kayaking eco tour with the areas most experienced tour guides. Your tour guide...

120 to 150 minutes • Free Cancellation
5.0 (160)
from
$85
Naples Guided Sunset Kayak Tour Activity

We are the only Kayak Tour Agency offering Sunset Tours at this location with the Hobie Pedal Mirage Drives. Whether you choose to paddle or …More

Likely to Sell Out
Likely to Sell Out
4.9 (17)

Naples Guided Sunset Kayak Tour Activity

We are the only Kayak Tour Agency offering Sunset Tours at this location with the Hobie Pedal Mirage Drives. Whether you choose to paddle or...

3 hours • Free Cancellation
4.9 (17)
from
$85
Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic …More

Likely to Sell Out
Likely to Sell Out
4.9 (18)

Tiki Pub Glow Party Cruise (Adults only)

Light up the night on Fort Myers! Sail the backwaters of Fort Myers Beach under shimmering stars, sipping on your BYOB drinks. Experience the magic...

2 hours • Free Cancellation
4.9 (18)
from
$80
Dolphin and Manatee Adventure Tour of Fort Myers

Come join us for a once in a lifetime experience that is great for all skill levels. There are only a few places on earth …More

Likely to Sell Out
Likely to Sell Out
4.9 (2,972)

Dolphin and Manatee Adventure Tour of Fort Myers

Come join us for a once in a lifetime experience that is great for all skill levels. There are only a few places on earth...

2 hours • Free Cancellation
4.9 (2,972)
from
$77
Dolphin and Shelling Cruise Tour at Fort Myers Beach

- Do it all on this trip, look for shells, see dolphins, and spend time in nature. Led by certified naturalists or a biologist, each …More

4.9 (194)

Dolphin and Shelling Cruise Tour at Fort Myers Beach

- Do it all on this trip, look for shells, see dolphins, and spend time in nature. Led by certified naturalists or a biologist, each...

3 hours • Free Cancellation
4.9 (194)
from
$75
Southwest Florida Sunset Sail

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The …More

5.0 (508)

Southwest Florida Sunset Sail

SWFL sunsets are the best, and there is no better place to watch them than from the deck of our 36ft. Sailing Catamaran, "Copacetic". The...

2 hours • Free Cancellation
5.0 (508)
from
$70
Copacetic Day Sail

Come sail with us in the mid morning or afternoon and take in the serenity that our pristine emerald waters can provide! Dolphins, Manatees, Sea …More

4.8 (278)

Copacetic Day Sail

Come sail with us in the mid morning or afternoon and take in the serenity that our pristine emerald waters can provide! Dolphins, Manatees, Sea...

2 hours • Free Cancellation
4.8 (278)
from
$70
Sunset Dolphin Cruise with Sanibel Lighthouse Views

While enjoying a complimentary alcoholic or nonalcoholic beverage we will cruise the back waters of Fort Myers Beach. During the cruise you may spot various …More

Likely to Sell Out
Likely to Sell Out
4.8 (457)

Sunset Dolphin Cruise with Sanibel Lighthouse Views

While enjoying a complimentary alcoholic or nonalcoholic beverage we will cruise the back waters of Fort Myers Beach. During the cruise you may spot various...

1 hour 30 minutes • Free Cancellation
4.8 (457)
from
$70
Fort Myers Beach Sunset and Dolphin Watching Cruise

Join us for a Fort Myers Beach sunset cruise and enjoy a relaxing evening on the water with stunning views of the Gulf and Sanibel …More

Likely to Sell Out
Likely to Sell Out
5.0 (300)

Fort Myers Beach Sunset and Dolphin Watching Cruise

Join us for a Fort Myers Beach sunset cruise and enjoy a relaxing evening on the water with stunning views of the Gulf and Sanibel...

1 hour 30 minutes • Free Cancellation
5.0 (300)
from
$70
Guided Kayak Eco Tour - Bunche Beach

Paddle through mangrove tunnels, explore shallow bays, and cruise along the beach, all while taking in the wide variety of wildlife that makes this part …More

4.9 (241)

Guided Kayak Eco Tour - Bunche Beach

Paddle through mangrove tunnels, explore shallow bays, and cruise along the beach, all while taking in the wide variety of wildlife that makes this part...

150 to 180 minutes • Free Cancellation
4.9 (241)
from
$70
Guided Kayak Dolphin Eco Tour in Pelican Bay

This tour will take you along an all natural shoreline of beaches and Mangroves. Here you can explore some of the mangrove lined canals, creeks, …More

Likely to Sell Out
Likely to Sell Out
4.8 (24)

Guided Kayak Dolphin Eco Tour in Pelican Bay

This tour will take you along an all natural shoreline of beaches and Mangroves. Here you can explore some of the mangrove lined canals, creeks,...

150 to 180 minutes • Free Cancellation
4.8 (24)
from
$70
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play …More

Likely to Sell Out
Likely to Sell Out
4.9 (149)

2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)

Tiki Pub is a great way to create memories on the water! Enjoy ice cold beverages (BYOB), take pics, get some sun, make friends, play...

2 hours • Free Cancellation
4.9 (149)
from
$69

Frequently Asked Questions

These answers are based on answers previously given to Cool SWFL customers' questions.

Recent tour reviews
A Most Enjoyable Trip
New York City
Kayak Eco Tour in Don Pedro Island
Lamboid2, Sep 2026
A Most Enjoyable Trip
Jeff, our guide for the morning made the whole trip for us. He was engaging, knowledgeable, funny but above friendly who gladly gave his time to talk about the wildlife we encountered. The area is beautiful, the paddling not too hard and the wildlife varied. The trip rounded off with Jeff finding us a mother dolphin with her two very young babies teaching them how to catch fish. Mesmerising! Would definitely recommend as we found the whole outfitters to be friendly and efficient
Read more
Highly recommend this cruise.
New York City
Sunset Dolphin Cruise with Sanibel Lighthouse Views
linaw700, Sep 2026
Highly recommend this cruise.
The cruise was very good. Our guide was knowledgeable and made the cruise enjoyable. I would definitely do this again with others.
Read more
Girls trip adventure
New York City
Dolphin and Manatee Adventure Tour of Fort Myers
susanbK8746WC, Sep 2026
Girls trip adventure
We had an excellent kayak trip! Our guide was fun, knowledgeable, and helpful!
Read more
Awesome ride
New York City
Sunset Dolphin Cruise with Sanibel Lighthouse Views
Maps220877, Sep 2026
Awesome ride
Awesome experience. Dan and Deacon were excellent guides. Lots of dolphins
Read more
The cruise was awesome
New York City
Southwest Florida Sunset Sail
F1799AKtodda, Sep 2026
The cruise was awesome
We will never use Cool SWFL again.!👎👎👎👎👎
Read more
Paradise on the bay and gulf!
New York City
Copacetic Day Sail
S1171LLannettem, Sep 2026
Paradise on the bay and gulf!
Fantastic experience! Great sailing and we got to see all the sites, and the dolphins were amazing and plentiful! Rainbows to end our cruise! Very friendly and allow you to sail too!
Read more
Excellent highly recommend
New York City
Fort Myers Beach 1.5hr Jet Ski Dolphin Tour
cticich14, Sep 2026
Excellent highly recommend
Tyson was excellent highly recommend this guy when you go on a dolphin tour very knowledgeable on how to get the dolphins once they are spotted very knowledgeable on the waterways also
Read more
Tour experience
New York City
Dolphin and Manatee Adventure Tour of Fort Myers
92gwenf, Sep 2026
Tour experience
Brady was an awesome guide. Very informative. Made the trip entertaining
Read more
Fun sunset cruise!
New York City
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
LadyDi570617, Sep 2026
Fun sunset cruise!
Was loads of fun! Cody was awesome kept everyone engaged!
Read more
So fun!!
New York City
Kayak Eco Tour in Don Pedro Island
irishpostal, Sep 2026
So fun!!
We had a wonderful experience. The young man there was super helpful and knowledgeable. We were challenged at the mangrove and worked hard there. We didn’t see much that day but all in all a great time!
Read more
Lots of fun and informative
New York City
2 hour Tiki Pub Sensational Dolphin Sunset Cruise (Adults only)
annemarien911, Sep 2026
Lots of fun and informative
Captain Cayla was amazing. She was very informative and lots of fun. This was the second time she captained the Tiki boat for us and my husband and I would and will do it again! She went out of her way to get close enough to the dolphins to take pictures!
Read more
Fun.
New York City
Ft Myers Beach 3 Hour Tiki Pub Tropical Sandbar Getaway Cruise
Dennis_T, Sep 2026
Fun.
Kayla was an amazing captain. Sea Turtles, manatees dolphins. Partied in the sand bar. Saw some star fish. So fun.
Read more
great fishing- plenty of Largemouth bass caught
New York City
Private Lake Okeechobee Bass Charter Near Naples
fedrika2026, Sep 2026
great fishing- plenty of Largemouth bass caught
Been on a few fishing trips out of Lake Okeechobee but can highly recommend Bass Online. This is the second time we have been out with Capt. Mark. We took 12- and 15-year-olds with us and caught a lot of big bass. It is still early season, but with approximately 30 plus caught in the 4 hours, there were happy customers all round. I've had experience with some fishing charter companies that only seem to care about the money and have some questionable practices, but I'm pleased to say that Bass Online charters do not fall into this category. I would, and have, recommended Bass Online to others.
Read more
Fantastic experience
New York City
2.5 hr Sailboat Tour aboard Orion’s Child
A8076HVjeffreym, Sep 2026
Fantastic experience
Always a great sail with Orions Child. Captain Dan and Diane are the best. We have been several times and will be back.
Read more
Excellent Trip
New York City
Private Lake Okeechobee Bass Charter Near Naples
nicholaslQ5003GV, Sep 2026
Excellent Trip
An excellent 6 hr and well worth every penny, Paul the Captain was very patient with both us and our 12-year-old; if you've never fished before, they will show you how, and we caught a lot of Largemouth bass...great fun for everyone, if you want to go fishing, go with Paul on the Bass Online.
Read more
Great Dolphin Watching Ride
New York City
Fort Myers Beach 1.5hr Jet Ski Dolphin Tour
198jamessf, Sep 2026
Great Dolphin Watching Ride
Great trip. the staff at the booth was very friendly and accommodating to us. We had to reschedule due to inclement weather in the Gulf but came back the next day for our dolphin tour. It was great, saw several dolphins and got to see a lot of the bay side of FMB. Wed definitely do it again. highly recommend.
Read more
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